Carbonic acid allyl ester (2R,3S,5R)-5-(6-allyloxycarbonylamino-purin-3-yl)-2-{allyloxy-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester | 181262-78-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: Carbonic acid allyl ester (2R,3S,5R)-5-(6-allyloxycarbonylamino-purin-3-yl)-2-{allyloxy-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-prop-2-enoxyphosphoryl]oxymethyl]-5-[6-(prop-2-enoxycarbonylamino)purin-3-yl]oxolan-3-yl] prop-2-enyl carbonate
• CAS: 181262-78-2
• 化学式: C₃₁H₃₈N₇O₁₄P
• 分子量: 763.655
• InChiKey: GIHCSEPVFOVXHM-FCRRCTENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  53.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  255.77
• 氢给体数：
  3.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid allyl ester (2R,3S,5R)-5-(6-allyloxycarbonylamino-purin-3-yl)-2-{allyloxy-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 正丁胺 、 三苯基膦 作用下， 以 甲酸 为溶剂， 反应 1.0h， 生成 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-3-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Methodology for the Synthesis of Dinucleoside Monophosphates Containing A 2′-Deoxy-3-Isoadenosine Unit: 3-iso-dApT and Tp(3-iso-dA)

  摘要：

  2'-Deoxy-3-isoadenylyl(3'-5')thymidine and thymidylyl-(3'-5')-2'-deoxy-3-isoadenosine have been synthesized by mild protection/deprotection methodology that circumvents facile N3-Cl' hydrolytic cleavage of the 2'-deoxy-3-isoadenosine moiety.

  DOI：

  10.1080/07328319608002437
• 作为产物：
  描述：

  3-[beta-D-Ribofuranosyl]-adenine 在 四氮唑 、 叔丁基过氧化氢 、 二氯乙酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 Bu₄SnCl 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 50.53h， 生成 Carbonic acid allyl ester (2R,3S,5R)-5-(6-allyloxycarbonylamino-purin-3-yl)-2-{allyloxy-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxy]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Methodology for the Synthesis of Dinucleoside Monophosphates Containing A 2′-Deoxy-3-Isoadenosine Unit: 3-iso-dApT and Tp(3-iso-dA)

  摘要：

  2'-Deoxy-3-isoadenylyl(3'-5')thymidine and thymidylyl-(3'-5')-2'-deoxy-3-isoadenosine have been synthesized by mild protection/deprotection methodology that circumvents facile N3-Cl' hydrolytic cleavage of the 2'-deoxy-3-isoadenosine moiety.

  DOI：

  10.1080/07328319608002437